JPS62299817A - Oriented film material for liquid crystal display element - Google Patents

Oriented film material for liquid crystal display element

Info

Publication number
JPS62299817A
JPS62299817A JP14352186A JP14352186A JPS62299817A JP S62299817 A JPS62299817 A JP S62299817A JP 14352186 A JP14352186 A JP 14352186A JP 14352186 A JP14352186 A JP 14352186A JP S62299817 A JPS62299817 A JP S62299817A
Authority
JP
Japan
Prior art keywords
film material
acrylsiloxane
liquid crystal
films
polymer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
JP14352186A
Other languages
Japanese (ja)
Inventor
Mitsuru Kano
満 鹿野
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Alps Alpine Co Ltd
Original Assignee
Alps Electric Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Alps Electric Co Ltd filed Critical Alps Electric Co Ltd
Priority to JP14352186A priority Critical patent/JPS62299817A/en
Publication of JPS62299817A publication Critical patent/JPS62299817A/en
Pending legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G02OPTICS
    • G02FOPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333Constructional arrangements; Manufacturing methods
    • G02F1/1337Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films

Abstract

PURPOSE:To obtain an oriented film material which has excellent adhesiveness to glass, necessitates a relatively low temp. for a heat treatment, and has excellent orientability and orientation life by using an acrylsiloxane polymer introduced with an alkoxysilane group into the side chain of the main chain of acryl. CONSTITUTION:Transparent conductive films 13, 14 consisting of ITO films, etc., are respectively patterned and formed on the inside surfaces of a pair of substrates 11, 12 consisting of glass, etc., and oriented films 15, 16 are respectively formed further on the inside surfaces of the transparent conductive films 13, 14. A sealant is disposed to the peripheral edge and the two substrates 11, 12 are joined to constitute a cell. A liquid crystal compsn. 18 is sealed into the cell by which the above-mentioned display element is constituted. The oriented film material consisting of the acrylsiloxane polymer is used as at least one material of the oriented films 15, 16. For example, the acrylsiloxane oligomer in which the main chain of the acryl constitutes a copolymer of methyl methacrylate, butyl acrylate and styrene and the alkoxy silane group is bonded to the side chain thereof is used as the acrylsiloxane polymer.

Description

【発明の詳細な説明】 3、発明の詳細な説明 「技術分野」 本発明は、液晶表示素子用配向膜材料に係り、特に強誘
電性液晶を用いた高速光スイッチング素子などに好適な
配向膜材料に関する。
[Detailed Description of the Invention] 3. Detailed Description of the Invention [Technical Field] The present invention relates to an alignment film material for liquid crystal display elements, and in particular an alignment film suitable for high-speed optical switching elements using ferroelectric liquid crystals. Regarding materials.

「従来技術およびその問題点J 従来、液晶表示素子の配向膜材料としでは、有機シラン
系の界面活性剤や、ポリアミック酸の架橋重合体である
ポリイミド、各種ナイロン、あるいはアクリル樹脂など
が用いられでいる。
"Prior Art and its Problems J Conventionally, organic silane surfactants, polyimide which is a cross-linked polymer of polyamic acid, various nylons, or acrylic resins have been used as alignment film materials for liquid crystal display elements. There is.

有機シラン系の界面活性剤は、簡便に膜形成ができると
いう長所があるが、配向安定性が悪いという問題点があ
った。
Organic silane surfactants have the advantage of being easy to form a film, but have the problem of poor alignment stability.

また、ポリイミドは、配向性がよいという長所があるが
、湿気に敏感であり、ガラス基板との接着性がやや弱く
、300℃前後の高温熱処理が必要となる問題点があっ
た。
Further, although polyimide has the advantage of good orientation, it is sensitive to moisture, has somewhat weak adhesion to glass substrates, and has the problem of requiring high-temperature heat treatment at around 300°C.

ざらに、各種ナイロンは、配向性がよく、熱処理温度が
低くてよいという長所があるが、ガラス基板との接着性
が弱いという問題点があった。
Generally speaking, various types of nylon have the advantage of having good orientation and requiring low heat treatment temperatures, but they have the problem of weak adhesion to glass substrates.

ざらにまた、アクリル樹脂は、配向性がよく、熱処理温
度が比較的低温でずむという長所があるが、ガラス基板
との接着性が弱く、湿気に弱いという問題点があった。
Additionally, acrylic resins have the advantage of good orientation and can be heat-treated at a relatively low temperature, but they have problems such as poor adhesion to glass substrates and susceptibility to moisture.

このように、これまでの配向膜材料はそれぞれ長所と短
所を有しでおり、あらゆる特性において満足し得るもの
はなかった。
As described above, each of the existing alignment film materials has its advantages and disadvantages, and none of them has been satisfactory in all characteristics.

近年、スメクティックC相などの強誘電性液晶を用いた
高速光スイッチング素子などが注目されているが、これ
らの素子はセルギャップが2 um程度と極めて薄く、
熱処理温度をあまり高めることができないという制限が
ある。
In recent years, high-speed optical switching devices using ferroelectric liquid crystals such as smectic C-phase have attracted attention, but these devices have extremely thin cell gaps of about 2 um.
There is a limitation in that the heat treatment temperature cannot be increased too much.

この点、ナイロン、アクリル樹脂などは、比較的低温(
200℃以下)の処理で膜形成できるのであるが、ガラ
スとの接着性が悪いという問題点があった。
In this respect, materials such as nylon and acrylic resin are relatively low temperature (
Although it is possible to form a film by processing at temperatures below 200° C., there is a problem in that the adhesion to glass is poor.

「発明の目的」 本発明の目的は、ガラスとの接着性に優れ、熱処理温度
も比較的低温ですみ、さらに配向性、配向寿命にも優れ
た液晶表示素子用配向膜材料を提供することにある。
"Objective of the Invention" The object of the present invention is to provide an alignment film material for a liquid crystal display element that has excellent adhesion to glass, requires relatively low heat treatment temperature, and has excellent alignment properties and alignment life. be.

「発明の構成」 本発明の液晶表示素子用配向膜材料は、アクリル主鎖の
側鎖にアルコキシシラン基を導入したアクリルシロキサ
ンポリマーからなることを特徴とする。
"Structure of the Invention" The alignment film material for a liquid crystal display element of the present invention is characterized by being made of an acrylic siloxane polymer in which an alkoxysilane group is introduced into the side chain of an acrylic main chain.

このように、本発明の配向膜材料は、アクリル主鎖を有
するので、アクリル樹脂の長所である良好な配向性を有
している。また、アクリル主鎖に、ガラスとカップリン
グ可能なアルコキシシラン基を導入したので、ガラスと
の接着性が改善される。さらに、空気中の微量の水分と
反応して縮合反応により架橋するので、比較的低温で硬
化できる。そ()で、分子間に安定なシロキサン結合を
形成するので、耐熱、耐温性に優れている。
As described above, since the alignment film material of the present invention has an acrylic main chain, it has good alignment, which is an advantage of acrylic resin. Furthermore, since an alkoxysilane group capable of coupling with glass is introduced into the acrylic main chain, adhesion with glass is improved. Furthermore, since it reacts with a small amount of moisture in the air and crosslinks through a condensation reaction, it can be cured at a relatively low temperature. Because it forms stable siloxane bonds between molecules, it has excellent heat resistance and temperature resistance.

このアクリルシロキサンポリマーは、第2図に示すよう
に、アクリル主鎖21の側鎖に、アルコキシシラン基2
2が導入されててきている。この場合、アクリル主鎖2
1は、メチルメタアクリレートに代表されるアルキルメ
タアクリレートや、ブチルメタアクリレートに代表され
るアルキルアクリレートや、スチレンに代表される芳香
族ビニルなどの重合体あるいは共重合体からなっている
。また、アルコキシシラン基22は、例えばトリメトキ
シシラン、トリエトキシシラン、トリフェニルオキシシ
ランなどからなっている。
As shown in FIG. 2, this acrylic siloxane polymer has two alkoxysilane groups in the side chain of the acrylic main chain 21.
2 has been introduced. In this case, the acrylic main chain 2
1 is made of a polymer or copolymer such as an alkyl methacrylate typified by methyl methacrylate, an alkyl acrylate typified by butyl methacrylate, or an aromatic vinyl typified by styrene. Further, the alkoxysilane group 22 is made of, for example, trimethoxysilane, triethoxysilane, triphenyloxysilane, or the like.

このアクリルシロキサンポリマーは、第2図に示した構
造のオリゴマーを架橋重合させることによって硬化させ
ることかできる。その硬化機構は、第3図に示されでい
る。すなわち、同図(a)に示すように、アルコキシシ
ラン基(−3t(OR)3)が空気中の水分(H2O)
と反応しで、シラノール(−Si(叶)3)か形成され
る。そして、同図(b)に示すように、このシラノール
どうしが自己縮合してシロキサン結合(−Si−0−8
i−)を形成することにより、架橋される。また、同図
(C)に示すように、このシラノールとアルコキシシラ
ン基とが反応してシロ主サン結合を形成することによっ
ても架橋する。こうして、アルコキシシラン基を架橋さ
せることにより、硬化膜を得ることができる。
This acrylic siloxane polymer can be cured by crosslinking polymerization of an oligomer having the structure shown in FIG. The curing mechanism is shown in FIG. That is, as shown in the same figure (a), the alkoxysilane group (-3t (OR)
By reacting with, silanol (-Si(Kano)3) is formed. Then, as shown in the same figure (b), these silanols self-condense and siloxane bonds (-Si-0-8
i-) is crosslinked. In addition, as shown in FIG. 3(C), crosslinking also occurs when the silanol and the alkoxysilane group react to form a silo-main bond. By crosslinking the alkoxysilane groups in this manner, a cured film can be obtained.

この硬化反応は、原則として水分が存在すれば常温でも
進行するのであるが、実用的な硬化速度を得るためには
、150℃前後で20〜30分程度加熱処理することが
好ましい。また、硬化触媒として、硫酸、リン酸、リン
酸ハライド、ホスホニトリルハライト、ジアルキルフォ
スファイト、三フッ化ホウ素、有機酸ハライド、ゼオラ
イト、トリエチルアミン等の塩基、金属化合物などを添
加することにより、より硬化速度を速めることができる
In principle, this curing reaction will proceed even at room temperature in the presence of moisture, but in order to obtain a practical curing rate, it is preferable to perform a heat treatment at around 150° C. for about 20 to 30 minutes. In addition, by adding bases such as sulfuric acid, phosphoric acid, phosphoric acid halide, phosphonitrile halide, dialkyl phosphite, boron trifluoride, organic acid halide, zeolite, triethylamine, etc., and metal compounds as curing catalysts, even more Curing speed can be increased.

本発明においでは、第2図に示した構造のオリゴマーを
キシレン等の溶媒に溶がし、これを透明導電膜か形成さ
れた基板上にスピンコードなどの方法で塗布し、溶媒を
乾燥させた復、オリゴマーを架橋重合させることにより
、配向膜を形成することができる。なお、この配向膜に
は、必要に応じてラビング処理を行なう。
In the present invention, an oligomer having the structure shown in Figure 2 is dissolved in a solvent such as xylene, and this is applied onto a substrate on which a transparent conductive film is formed by a method such as a spin cord, and the solvent is dried. An alignment film can be formed by cross-linking polymerizing the oligomer. Note that this alignment film is subjected to a rubbing treatment if necessary.

「発明の実施例」 第1図には、本発明の配向膜材料が適用される液晶表示
素子の一例が示されでいる。
"Embodiments of the Invention" FIG. 1 shows an example of a liquid crystal display element to which the alignment film material of the present invention is applied.

すなわち、ガラス等からなる一対の基板11.12の内
面に、ITO膜などの透明導電膜13.14がそれぞれ
パターン化されで形成され、この透明導電膜13.14
のさらに内面に、配向膜15.16がそれぞれ形成され
る。そして、周縁部にシール剤17を配置して内基板1
1.12を接合し、セルを構成する。ざらに、このセル
内に、液晶組成物18を封入しで構成されでいる。アク
リルシロキサンポリマーからなる本発明の配向膜材料は
、上記配向膜15.16の少なくとも一方の材料としで
用いられる。なお、上記配向膜15.16の少なくとも
一方は、ラビング処理して一軸配向制御する場合が多い
That is, a patterned transparent conductive film 13.14 such as an ITO film is formed on the inner surface of a pair of substrates 11.12 made of glass or the like.
Furthermore, alignment films 15 and 16 are formed on the inner surfaces of the substrates, respectively. Then, a sealant 17 is placed on the periphery of the inner substrate 1.
1.12 are joined to form a cell. Roughly speaking, a liquid crystal composition 18 is sealed in this cell. The alignment film material of the present invention made of an acrylic siloxane polymer is used as a material for at least one of the alignment films 15 and 16. Note that at least one of the alignment films 15 and 16 is often subjected to a rubbing treatment to control the uniaxial alignment.

実施例 アクリル主鎖がメチルメタクリレート、ブチルアクリレ
ート、スチレンの共重合体をなし、その側鎖にアルコキ
シシラン基を結合させたアクリルシロキサンオリゴマー
「カネカーゼムラツク」(商品名、鐘淵化学製、Gra
de No、YC3835) %キシレンに溶解し、キ
シレン濃度を98%とした溶液を調製する。
Example Acrylic siloxane oligomer ``Kanecase Murakku'' (trade name, manufactured by Kanekabuchi Chemical Co., Ltd., Gra
de No., YC3835) % xylene to prepare a solution with a xylene concentration of 98%.

次に、充分に水洗ずみのITO膜付きのガラス基板上に
前記溶液を塗布する。塗布は、スピンナーを用い、回転
数3000rpm 、約60秒で行なった。その後、基
板150℃で30分乾燥させて膜形成を行なった。形成
された膜は均一であり、膜厚約1000Aであった。こ
の基板を脱脂綿で軽く数回一方向にこすりラビングを行
なう。なお、うどング方向は、上下基板を貼り合せたと
き、ラビング方向がアンチパラレルとなるようにした。
Next, the solution is applied onto a glass substrate with an ITO film that has been thoroughly washed with water. The coating was carried out using a spinner at a rotation speed of 3000 rpm for about 60 seconds. Thereafter, the substrate was dried at 150° C. for 30 minutes to form a film. The formed film was uniform and had a thickness of about 1000 Å. Lightly rub this substrate in one direction several times with absorbent cotton. Note that the rubbing direction was such that when the upper and lower substrates were bonded together, the rubbing direction was antiparallel.

次に、市販の2 um粒径のアルミナ粉末を一方の基板
上に少量まきちらす。また、他方の基板には、エポキシ
系のシール剤をスクリーン印刷で周縁部に塗布し、その
後間基板を貼り合せでシール剤を140℃、30分の熱
処理で硬化させた。こうして得られたセルに、市販のS
mC”液晶組成物rS−10144(商品名、チッソ製
)を注入し、注入口をuv硬化樹脂にで封止した。
Next, a small amount of commercially available alumina powder with a particle size of 2 um is sprinkled onto one of the substrates. Furthermore, an epoxy sealant was applied to the peripheral edge of the other substrate by screen printing, and then the intervening substrates were bonded together and the sealant was cured by heat treatment at 140° C. for 30 minutes. Commercially available S
mC'' liquid crystal composition rS-10144 (trade name, manufactured by Chisso) was injected, and the injection port was sealed with UV curing resin.

このようにしで形成した高速光スイッチング素子は、1
00倍の顕微鏡観察の結果、配向性が極めて良好であっ
た。すなわち、従来優れているといわれているポリイミ
ド配向膜の場合と比べて同等以上であった。ざらに、こ
の高速光スイッチング素子を用いで、120℃、2気圧
の条件下でプレッシャークツカー試験を行なったところ
、同様にして作成したアクリル系配向膜のセルと比べで
、配向性の劣化スピードは約174Cあり、極めで優れ
た配向寿命を有することかわかった。
The high-speed optical switching element formed in this way has 1
As a result of microscopic observation at 00x magnification, the orientation was extremely good. That is, it was equivalent to or better than the case of a polyimide alignment film, which is said to be excellent in the past. Roughly speaking, when we conducted a pressure tester using this high-speed optical switching element under the conditions of 120°C and 2 atmospheres, we found that the speed of deterioration of the alignment was compared to a cell made in the same way using an acrylic alignment film. was approximately 174C, and was found to have an extremely excellent alignment life.

「発明の効果」 以上説明したよう1こ、本発明によれば、アクリル主鎖
の側鎖にアルコキシシラン基を導入したアクリルシロキ
サンポリマーからなるので、ガラスとの接着′I!に優
れ、熱処理温度も比較的低温ですみ、さらに配向性、配
向寿命にも優れた配向膜材料を得ることができる。
"Effects of the Invention" As explained above, according to the present invention, since it is made of an acrylic siloxane polymer in which alkoxysilane groups are introduced into the side chains of the acrylic main chain, it has excellent adhesion to glass! It is possible to obtain an alignment film material that has excellent properties, requires only a relatively low heat treatment temperature, and has excellent alignment properties and alignment life.

【図面の簡単な説明】[Brief explanation of the drawing]

第1図は本発明の配向膜材料が適用された液晶表示素子
の一例を示す断面図、第2図は本発明の配向膜材料の分
子構造を示す説明図、第3図(a) 、(b) 、(c
)は本発明の配向膜材料の硬化機構を示す説明図である
。 図中、21はアクリル主鎖、22はアルコキシシラン基
である。 特許出願人  アルプス電気株式会社 第2図
FIG. 1 is a cross-sectional view showing an example of a liquid crystal display element to which the alignment film material of the present invention is applied, FIG. 2 is an explanatory diagram showing the molecular structure of the alignment film material of the present invention, and FIGS. b) , (c
) is an explanatory diagram showing the curing mechanism of the alignment film material of the present invention. In the figure, 21 is an acrylic main chain, and 22 is an alkoxysilane group. Patent applicant Alps Electric Co., Ltd. Figure 2

Claims (1)

【特許請求の範囲】[Claims] アクリル主鎖の側鎖にアルコキシシラン基を導入したア
クリルシロキサンポリマーからなることを特徴とする液
晶表示素子用配向膜材料。
An alignment film material for liquid crystal display elements, characterized by being made of an acrylic siloxane polymer in which an alkoxysilane group is introduced into the side chain of an acrylic main chain.
JP14352186A 1986-06-19 1986-06-19 Oriented film material for liquid crystal display element Pending JPS62299817A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP14352186A JPS62299817A (en) 1986-06-19 1986-06-19 Oriented film material for liquid crystal display element

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP14352186A JPS62299817A (en) 1986-06-19 1986-06-19 Oriented film material for liquid crystal display element

Publications (1)

Publication Number Publication Date
JPS62299817A true JPS62299817A (en) 1987-12-26

Family

ID=15340671

Family Applications (1)

Application Number Title Priority Date Filing Date
JP14352186A Pending JPS62299817A (en) 1986-06-19 1986-06-19 Oriented film material for liquid crystal display element

Country Status (1)

Country Link
JP (1) JPS62299817A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0421435A2 (en) * 1989-10-03 1991-04-10 Nippon Oil And Fats Company, Limited Ultrathin membrane of polymethacrylate or polycrotonate and device provided with ultrathin membrane
JP2016170389A (en) * 2015-03-12 2016-09-23 エルジー ディスプレイ カンパニー リミテッド Liquid crystal display element and manufacturing method for the same
US10558084B2 (en) 2016-03-11 2020-02-11 Lg Display Co., Ltd. Liquid crystal display device and method of fabricating the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0421435A2 (en) * 1989-10-03 1991-04-10 Nippon Oil And Fats Company, Limited Ultrathin membrane of polymethacrylate or polycrotonate and device provided with ultrathin membrane
JP2016170389A (en) * 2015-03-12 2016-09-23 エルジー ディスプレイ カンパニー リミテッド Liquid crystal display element and manufacturing method for the same
US10558084B2 (en) 2016-03-11 2020-02-11 Lg Display Co., Ltd. Liquid crystal display device and method of fabricating the same

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